John Key resignation: The enduring images

It's been a long innings for John Key, who announced his resignation on Monday after nearly three terms as New Zealand Prime Minister.

Here's a collection of memorable images of our outgoing leader.

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Mr Key, as the fresh-faced leader of the National Party, won the New Zealand general election in 2008. His now-famous son Max was just 13 years old.

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Mr Key has had a number of 'bromances' with other world leaders. He has golfed with US President Barack Obama in Hawaii and gone kayaking with Australian Prime Minister Malcolm Turnbull.

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He also had a good friendship with former All Black captain Richie McCaw, with whom he shared the infamous three-way handshake at the All Blacks' World Cup victory in 2011.

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In 2011 Mr Key strutted the catwalk showing off the Rugby World Cup volunteer uniform.

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In 2014 National won its third term as New Zealand's Government, with Mr Key continuing as Prime Minister.

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Mr Key initiated a referendum on whether New Zealand should get a new flag. He was a strong advocate for the Lockwood design that included a white fern on a black and blue background. Here he is wrapped in New Zealand's official 'blue ensign' flag.

He has been a supporter of the Big Gay Out, which he attended again in 2016. Here he is with a Big Gay Out party-goer, also wrapped in a flag.

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Mr Key spent much of 2016 campaigning for his old foe, former Labour leader Helen Clark, in her bid for leadership of the United Nations.